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885270-73-5

(3-AMINO-4-CHLORO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER synthesis

4synthesis methods
-

Yield:885270-73-5 83%

Reaction Conditions:

in dichloromethane at 20; for 48 h;

Steps:

31.a

A solution of di-f-butyl dicarbonate (3.37 g, 15.4 mmol) in dichloromethane (8 mL) was added over 5 min to a stirred suspension of 2-chloro-1 ,3-benzenediamine (2.00 g, 14.0 mmol) in dichloromethane (22 mL) at room temperature. After stirring 48 h, the solvent was removed under reduced pressure and the residue slurried in dichloromethane (15 mL), then filtered, washed with 20% dichloromethane/hexane and dried. The filtrate was evaporated to dryness under reduced pressure and a second crop of product obtained by recrystallisation from 2:1 hexane:ether. Both crops were combined to give the title compound (2.83 g, 83%) as a solid. 1 H NMR (400MHz, DMSO-d6 ) δ 1.46 (s, 9H), 5.25 (br s, 2H), 6.56 (dd, J = 8.7, 2.4 Hz, 1 H), 7.01 (d, J = 8.6 Hz, 1 H),7.08 (d, J = 2.0 Hz, 1 H), 9.18 (s, 1 H).

References:

WO2006/127458,2006,A2 Location in patent:Page/Page column 58

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